Cu/Pd Synergistic Dual Catalysis: Asymmetric α‐Allylation of an α‐CF<sub>3</sub> Amide

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  • Akira Saito
    Institute of Microbial Chemistry (BIKAKEN) Tokyo 3-14-23 Kamiosaki, Shinagawa-ku Tokyo 141-0021 Japan
  • Naoya Kumagai
    Institute of Microbial Chemistry (BIKAKEN) Tokyo 3-14-23 Kamiosaki, Shinagawa-ku Tokyo 141-0021 Japan
  • Masakatsu Shibasaki
    Institute of Microbial Chemistry (BIKAKEN) Tokyo 3-14-23 Kamiosaki, Shinagawa-ku Tokyo 141-0021 Japan

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<jats:title>Abstract</jats:title><jats:p>Despite the burgeoning demand for fluorine‐containing chemical entities, the construction of CF<jats:sub>3</jats:sub>‐containing stereogenic centers has remained elusive. Herein, we report the strategic merger of Cu<jats:sup>I</jats:sup>/base‐catalyzed enolization of an α‐CF<jats:sub>3</jats:sub> amide and Pd<jats:sup>0</jats:sup>‐catalyzed allylic alkylation in an enantioselective manner to deliver chiral building blocks bearing a stereogenic carbon center connected to a CF<jats:sub>3</jats:sub>, an amide carbonyl, and a manipulable allylic group. The phosphine complexes of Cu<jats:sup>I</jats:sup> and Pd<jats:sup>0</jats:sup> engage in distinct catalytic roles without ligand scrambling to render the dual catalysis operative to achieve asymmetric α‐allylation of the amide. The stereoselective cyclization of the obtained α‐CF<jats:sub>3</jats:sub>‐γ,δ‐unsaturated amides to give tetrahydropyran and γ‐lactone‐fused cyclopropane skeletons highlights the synthetic utility of the present catalytic method as a new entry to non‐racemic CF<jats:sub>3</jats:sub>‐containing compounds.</jats:p>

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